Not that I know what's going on, but it looks like the upgrade happily chugged along using the 3.2 version of rsa... and then decided to remove it (possibly wanting to upgrade to 3.3) and decided that it was unhappy that 3.2 wasn't available.

OctoPrint 1.3.9 and later include a couple of dependency updates whose update during switch to 1.3.9 or later are known to trigger an "update failed" message within OctoPrint's update dialog: The update did in fact succeed and the issue lies with...